Synthesis of Amide Class Heterocyclic Ketene Aminals

doi:10.6023/cjoc201607002

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 166-175.DOI: 10.6023/cjoc201607002 Previous Articles Next Articles

ARTICLE

酰胺类杂环烯酮缩胺的合成

罗大云, 崔时胜, 胡兴梅, 林军, 严胜骄

云南大学化学科学与工程学院教育部自然资源药物化学重点实验室昆明 650091

收稿日期:2016-07-02 修回日期:2016-08-25 发布日期:2016-09-08
通讯作者: 林军, 严胜骄 E-mail:linjun@ynu.edu.cn;yansj@ynu.edu.cn
基金资助:
国家自然科学基金（Nos. 21362042，U1202221，21662042）、云南省后备人才（No. 2012HB001）、云南大学青年英才计划（No. XT412003）资助项目.

Synthesis of Amide Class Heterocyclic Ketene Aminals

Luo Dayun, Cui Shisheng, Hu Xingmei, Lin Jun, Yan Shengjiao

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091

Received:2016-07-02 Revised:2016-08-25 Published:2016-09-08
Supported by:
Project supported by the National Natural Science Foundation of China(Nos. 21362042, U1202221, 21662042), the Talent Found in Yunnan Province(No. 2012HB001), and the Excellent Young Talents, Yunnan University(No. XT412003).

In this paper,a concise protocol for synthesis of possess potential pharmacological active amide class heterocyclic ketene aminals(HKAs) has been developed,which based on the six or seven-membered HKAs 1~2,using aryl isocyanate 4 as acylation agent.The regioselective acylation reaction of HKAs in 1,4-dioxane at room temperature gave compounds 5~6 with 90%~98% yields.However,the five-membered HKAs 3 and aryl isocyanate 4 reacted in 1,4-dioxane catalyzed by Cs₂CO₃ at room temperature to obtain compounds 7 in 78%~93% yields.

Key words: heterocyclic ketene aminals, isocyanate, regioselective, acylation reaction

Cite this article

Luo Dayun, Cui Shisheng, Hu Xingmei, Lin Jun, Yan Shengjiao. Synthesis of Amide Class Heterocyclic Ketene Aminals[J]. Chin. J. Org. Chem., 2017, 37(1): 166-175.

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酰胺类杂环烯酮缩胺的合成

Synthesis of Amide Class Heterocyclic Ketene Aminals

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